Ego is the Enemycame out exactly three months ago and I want to thank you for your support. The book was an immediate Wall Street Journal and USA Today bestseller (it also hit a few lists abroad) as well as receiving 4.6 out of 5 stars on Amazon with nearly 300 reviews so far. I want to thank you again for your support and especially the many of you who took part of the preorder campaign. I’m blown away by the support you all gave the book and I am having a wonderful time finishing the strategy calls with many of you who preordered more than 50 copies of the book.

Aside from the preorder campaign and the usual press around a book launch, I was interviewed at a number of podcasts and I thought I’d put a list together of some my favorite ones:

A few months ago, Chief Medicine Crow, one of the last remaining links to the Native American tribes of the Wild West died at age 102. He had grown up hearing stories about George Armstrong Custer from his grandfather, who’d been a scout for the doomed general at Little Bighorn in 1876. A soldier himself in the Second World War, Medicine Crow was one of the last Crow people to ever accomplish the four deeds required to be considering a war chief (command a war party, steal an enemy horse, touch an enemy without killing him and taking an enemy’s weapon).

He was a fascinating man, not just for what he did but also for what he represents to us now. He was, to use a phrase coined by Jason Kottke, a “human wormhole.” His unusual and long life is a reminder to how connected the past and present really are.

A curator at the Smithsonian described meeting Medicine Crow as “you’re shaking hands with the 19th century.” Which an amazing concept. A few intrepid historians on reddit recently discovered an even more amazing one, calculating that it would take a chain of just six individuals who shook hands with one another to connect Barack Obama to George Washington across the centuries (Obama ->Queen Elizabeth II -> Herbert Hoover -> William H. Taft -> Benjamin Harrison -> William Henry Harrison -> Benjamin Harrison V -> George Washington).

I’ve become fascinated with discovering and tracking some of these reminders. For some time now, I’ve kept a file of them on 4×6 notecards in my house. My friends and I email these moments to each other as we find them — some absurd (Oscar Wilde and Walt Whitman may have hooked up), coincidental (Orson Welles claimed to have been in the Biograph Theater in Chicago where John Dillinger was killed by the FBI) and some that are so unbelievable that they might just blow your mind (there’s a video from a 1956 CBS game show, “I’ve Got a Secret,” with a very old guest whose secret was that he was in Ford’s Theatre when Lincoln was assassinated. Appearing with him on the show? Lucille Ball.)

Here in modern life, it’s easy to think the past is dead and distant, until we bump up against the reality of Faulkner’s admonition that it’s not really even past. England’s government only recently paid off debts it incurred as far back as 1720 from events like the South Sea Bubble, the Napoleonic wars, the empire’s abolition of slavery, and the Irish potato famine — meaning that for more than a decade and a half of the twenty first century there was still a direct and daily connection to the eighteenth and nineteenth centuries. (The US is still paying pensions related to both the Civil War and the Spanish-American War.)

I’ll share a few more wormholes before I get to my point — because I promise there is more to this than just strange trivia.

Did you know that Tom Pratt, a football coach whose team the Arizona Cardinals narrowly missed going to the Super Bowl in 2015, was also on the coaching staff for the Kansas City Chiefs in the very first Super Bowl fifty years ago? Or that there are whales alive today who were born before Melville published Moby Dick? Or the world’s oldest tortoise, Jonathan, lives on an island in the Atlantic and is 183 years old? Or that President John Tyler, born in 1790, who took office just ten years after little Jonathan was born, still has living grandchildren?

War is perhaps the strangest source of these anomalies. Did you know that Winston Churchill and James Bond creator Ian Fleming’s father fought in the same unit in WWI? When Fleming’s father was killed, Churchill wrote his obituary. General Simon Bolivar Buckner was a Confederate general in the Civil War (he surrendered to Grant at Fort Donelson). His son Simon Bolivar Buckner Jr also became a General, and he died at Okinawa some 83 years later. General MacArthur — his father, Arthur MacArthur, Jr. — was a Civil War hero for the Union. Stonewall Jackson had a granddaughter who lived to be 104. She died in 1991.

In high school, a promising young student at the Virginia Military Institute named George Marshall petitioned the president for a military commission. Which President did the creator of the Marshall plan petition? William McKinley (just months before man’s life was cut short by an assassin’s bullet.) And most unbelievably, what of the fact that Robert Todd Lincoln was present as his father died of assassination, was at the train station with President James Garfield was assassinated, and was in attendance at the event in which McKinley was assassinated? Three assassinations, spread out over 40 years. Robert Todd Lincoln himself lived to be 82, dying in 1926. He could have read stories published by F. Scott Fitzgerald. He drove in a car. He talked on the telephone. He would have heard jazz music.

And these are just the events of the so called modern history.

We forget that woolly mammoths walked the earth while the pyramids were being built. We don’t realize that Cleopatra lived closer to our time than she did to the construction of those famous pyramids that marked her kingdom. We forget that Ovid and Jesus were alive at the same time. When British workers excavated the land in Trafalgar Square to build Nelson’s Column and its famous bronze lions, in the ground they found the bones of actual lions, who’d roamed that exact spot just a few thousand years before.

The effect of these stories — after the novelty wears off — is an intense humbling. We like to think that we are special — that we live in blessed, unprecedented times. It’s this self-absorption that disconnects us from the universe we belong to. It’s unthinking ego that makes us assume that because the photos of the past were in black and white, that the past itself was too.

Obviously, it wasn’t — their sky was the same color as ours (in some places brighter than ours), they bled the same way we did, and their cheeks got flushed just like ours do. “Think by way of example on the times of Vespasian,” wrote the wise Marcus Aurelius some 1900 years ago, “and you’ll see all these things: marrying, raising children, falling ill, dying, wars, holiday feasts, commerce, farming, flattering, pretending, suspecting, scheming, praying that others die, grumbling over one’s lot, falling in love, amassing fortunes, lusting after office and power. Now that life of theirs is dead and gone… the times of Trajan, again the same… ”

Again the same for us now. However much we celebrate our own exceptionalism.

In Goethe’s The Sorrows of Young Werther (which was a favorite of Napoleon’s) there is a scene in which Werther writes to a friend about his daily trip to a small, beautiful spring. He sees the young girls coming to gather water and thinks about how many generations have been doing that — have come and had same thoughts he is having. “When I sit there the patriarchal ways come vividly to life about me,” he says, “and I see them all, the ancestral fathers, making friends and courting by the spring, I sense the benevolent spirits that watch over springs and wells. Oh, anyone who cannot share this feeling must never have refreshed himself at a cool spring after a hard day’s summer walking.”

That’s the feeling most of us miss. Even if we don’t see it, it’s there. The whispers and the smoke and remnants never disappear. Goethe was born in 1749, wrote his first bestseller which contained those words in 1774 before America was a country, and would live well into the 19th century (overlapping briefly with Jonathan the Tortoise). A hundred years after that, another famous German writer, Stefan Zweig, would be stunned to find that his elderly upstairs neighbor was the daughter of Goethe’s doctor, who had vivid memories of meeting Goethe as a young girl. In fact, Goethe had attended her christening.

Sorry, I’m getting distracted. I have too many of these wormholes and I don’t know where to put them all.

Back to the point, Ernest Hemingway opens The Sun Also Rises with a bible verse: “One generation passeth, and another generation cometh; but the earth abideth forever. The sun also riseth, and the sun goeth down, and resteth to the place where he arose.” It was this passage, his editor would say that “contained all the wisdom of the ancient world.”

And what wisdom is that? That we all flow into each other as part of an endless stream (slavery, Louis C.K. observed is just two old ladies back to back). It seems slow and long to us because we’re in it. It seems distant to us because it wasn’t our problem, it wasn’t us that did that terrible deed we’d like to forget. In fact, time whips by in a blur. Wounds barely have time to heal. They don’t recognize the passing of generations. Because generations don’t really exist. It is instead an endless parade.

When I lived in New Orleans, my apartment was partitioned out of 19th century convent. When I would head uptown to write what became my first book, I’d hop on the longest continually running streetcar in the world — some 181 years it had been traveling the same tracks. How many millions of people had ridden those same rails? Sat, even, in the same seat. Tennessee Williams, Walker Percy, Shelby Foote, George Washington Cable, Edgar Degas — could have looked out these very windows. They, along with so many others not as easily remembered — but who lived and hustled and struggled just as I was trying to.

In moments like that, one cannot help but know what Pierre Hadot has referred to as the “oceanic feeling.” A sense of belonging to something larger, realizing that “human things are an infinitesimal point in the immensity.” And when one gets this feeling, we ask ourselves important questions about who we are and what we are doing.

On the other hand, nothing draws us away from those questions like material success — when we are always busy, stressed, put upon, distracted, reported to, relied on, apart from; when we’re wealthy or told that we’re important or powerful. Ego tells us that meaning comes from activity, that being the center of attention is the only way to matter. When we lack a connection to anything larger or bigger than us, it’s like a piece of our soul is gone. Like we’ve detached ourselves from the tradition we hail from — forgetting that we’re just like the people who came before us, and we’re but a brief stopover until the people just like you who will come after. The earth abideth forever, but we will come and go.

History on the other hand, gives us perspective. As I said, it has the power to humble us. Specifically, these wormholes — illustrating the “great span” as they do — are instant humility in bite-sized pieces. It’s proof that others have been here before you, generations of them, and that they can almost reach out and touch you. In those moments, we have a sense of the immensity of the world and also its smallness. Ego is impossible, because we realize, if only fleetingly, what Emerson meant when he said that “every man is a quotation from all his ancestors” or what John Muir tried to convey to us about his epic experiences in nature. Yes, we are small. We are also a piece of this great universe and a process.

Baldwin wrote that “if you can examine and face your life, you can discover the terms with which you are connected to other lives, and they can discover them, too.” I actually think it’s the reverse. If you can examine and face the connection between other lives, and other eras, only then can you begin to understand and appreciate your own.

Every man I meet is my master in some point, and in that I learn of him. — Ralph Waldo Emerson

The legend of Genghis Khan has echoed throughout history: A barbarian conqueror, fueled by bloodlust, terrorizing the civilized world. We have him and his Mongol horde traveling across Asia and Europe, insatiable, stopping at nothing to plunder, rape, and kill not just the people who stood in their way, but the cultures they had built. Then, not unlike his nomadic band of warriors, this terrible cloud simply disappeared from history, because the Mongols built nothing that could last.

Like all reactionary, emotional assessments, this could not be more wrong. For not only was Genghis Khan one of the greatest military minds who ever lived, he was a perpetual student, whose stunning victories were often the result of his ability to absorb the best technologies, practices, and innovations of each new culture his empire touched.

In fact, if there is one theme in his reign and in the several centuries of dynastic rule that followed, it’s this: appropriation.

Under Genghis Khan’s direction, the Mongols were as ruthless about stealing and absorbing the best of each culture they encountered as they were about conquest itself. Though there were essentially no technological inventions, no beautiful buildings or even great Mongol art, with each battle and enemy, their culture learned and absorbed something new.

Genghis Khan was not born a genius. Instead, as one biogra­pher put it, his was “a persistent cycle of pragmatic learning, experimental adaptation, and constant revision driven by his uniquely disciplined and focused will.” He was the greatest conqueror the world ever knew because he was more open to learning than any other conqueror has ever been.

Khan’s first powerful victories came from the reorganization of his military units, splitting his soldiers into groups of ten. This he stole from neighboring Turkic tribes, and unknowingly converted the Mongols to the decimal system.

Soon enough, their expanding empire brought them into contact with another “technology” they’d never experienced before: walled cities. In the Tangut raids, Khan first learned the ins and outs of war against fortified cities and the strategies critical to laying siege, and quickly became an expert. Later, with help from Chinese engineers, he taught his soldiers how to build siege machines that could knock down city walls. In his campaigns against the Jurched, Khan learned the importance of winning hearts and minds. By working with the scholars and royal family of the lands he conquered, Khan was able to hold on to and man­age these territories in ways that most empires could not.

Afterward, in every country or city he held, Khan would call for the smartest astrologers, scribes, doctors, thinkers, and advisers — anyone who could aid his troops and their efforts. His troops traveled with interrogators and translators for precisely this purpose.

It was a habit that would survive his death. While the Mongols themselves seemed dedicated almost solely to the art of war, they put to good use every craftsman, merchant, scholar, entertainer, cook, and skilled worker they came in contact with. The Mongol Empire was remarkable for its reli­gious freedoms, and most of all, for its love of ideas and con­vergence of cultures. It brought lemons to China for the first time, and Chinese noodles to the West. It spread Persian carpets, German mining technology, French metalworking, and Islam. The cannon, which revolutionized warfare, was said to be the resulting fusion of Chinese gunpowder, Mus­lim flamethrowers, and European metalwork. It was Mongol openness to learning and new ideas that brought them together.

As we first succeed, we will find ourselves in new situations, facing new problems. The freshly promoted soldier must learn the art of politics. The salesman, how to manage. The founder, how to delegate. The writer, how to edit others. The comedian, how to act. The chef turned restaurateur, how to run the other side of the house.

This is not a harmless conceit. The physicist John Wheeler, the physicist who helped develop the hydrogen bomb, once observed that “As our island of knowledge grows, so does the shore of our ignorance.” In other words, each victory and advancement that made Khan smarter also bumped him against new situations he’d never encountered before. It takes a special kind of humility to grasp that you know less, even as you know and grasp more and more. It’s remembering Socrates’ wisdom lay in the fact that he knew that he knew next to nothing.

With accomplishment comes a growing pressure to pre­tend that we know more than we do. To pretend we already know everything. Scientia infla (knowledge puffs up). That’s the worry and the risk — thinking that we’re set and secure, when in reality understanding and mastery is a fluid, con­tinual process.

The nine­-time Grammy– and Pulitzer Prize–winning jazz musician Wynton Marsalis once advised a promising young musician on the mind­set required in the lifelong study of music: “Humility engenders learning because it beats back the arrogance that puts blinders on. It leaves you open for truths to reveal themselves. You don’t stand in your own way. . . . Do you know how you can tell when someone is truly humble? I believe there’s one simple test: because they consistently observe and listen, the humble improve. They don’t assume, ‘I know the way.’” No matter what you’ve done up to this point, you better still be a student. If you’re not still learning, you’re already dying.

It is not enough only to be a student at the beginning. It is a position that one has to assume for life. Learn from everyone and everything. From the people you beat, and the people who beat you, from the people you dislike, even from your supposed enemies. At every step and every juncture in life, there is the opportunity to learn — and even if the lesson is purely remedial, we must not let ego block us from hearing it again.

It’s something I’ve had to learn as an author, personally. Just because one book does well, doesn’t mean that the next one will. It certainly doesn’t mean that everything that I’ll write is good or that I know everything there is to know about this profession either. Thinking that way is a recipe for falling off and disappointing both publishers and audiences. A better attitude is to start from scratch with each project — to focus on all there is left to learn and all the room we have left improve. That’s what I’ve tried to do with each subsequent project, including this most recent one (appropriately about ego).

Too often, convinced of our own intelligence or success, we stay in a comfort zone that ensures that we never feel stupid (and are never challenged to learn or reconsider what we know). It obscures from view various weaknesses in our under­ standing, until eventually it’s too late to change course. This is where the silent toll is taken.

Each of us faces a threat as we pursue our craft. Like sirens on the rocks, ego sings a soothing, validating song — which can lead to a wreck. The second we let the ego tell us we have graduated, learning grinds to a halt. That’s why UFC champion and MMA pioneer Frank Shamrock said, “Always stay a student.” As in, it never ends.

The solution is as straightforward as it is initially uncom­fortable: Pick up a book on a topic you know next to noth­ing about. Put yourself in rooms where you’re the least knowledgeable person. That uncomfortable feeling, that defensiveness that you feel when your most deeply held assumptions are challenged — what about subjecting your­self to it deliberately? Change your mind. Change your sur­roundings.

An amateur is defensive. The professional finds learning (and even, occasionally, being shown up) to be enjoyable; they like being challenged and humbled, and engage in education as an ongoing and endless process.

Most military cultures — and people in general — seek to impose values and control over what they encounter. What made the Mongols different was their ability to weigh each situation objectively, and if need be, swap out previous prac­tices for new ones. All great businesses start this way, but then something happens. Take the theory of disruption, which posits that at some point in time, every industry will be dis­rupted by some trend or innovation that, despite all the resources in the world, the incumbent interests will be incapable of responding to. Why is this? Why can’t businesses change and adapt? A large part of it is because they lost the ability to learn. They stopped being students. The second this happens to you, your knowledge becomes fragile.

“Among men who rise to fame and leadership two types are recognizable—those who are born with a belief in themselves and those in whom it is a slow growth dependent on actual achievement. To the men of the last type their own success is a constant surprise, and its fruits the more delicious, yet to be tested cautiously with a haunting sense of doubt whether it is not all a dream. In that doubt lies true modesty, not the sham of insincere self depreciation but the modesty of “moderation,” in the Greek sense. It is poise, not pose.” – B.H. Liddell Hart

When we’re young and just setting out in our careers we tend to assume that the greatest impediments to our progress and success are external to us. We blame our bosses and “the system” but we rarely think that we might be our own worst enemies, sabotaging ourselves right when we are beginning on our path.

Too often the obstacle that impedes our progress the most is internal—our own ego.

Yes, all of us, with all our talent and promise and potential, if we don’t control our ego, risk blowing up before we start. Talent, as Irving Berlin put it, is only the starting point. What we also need is self-management, self-control and humility.

Here are three ways that ego is the enemy of those important traits.

1. Talk, talk, talk.

At the beginning of any path, we’re excited and nervous. So we seek to comfort ourselves externally instead of inwardly. There’s a weak side to each of us, that—like a trade union—isn’t exactly malicious but at the end of the day still wants to get as much public credit and attention as it can for doing the least. That side we call ego.

The writer and former Gawker blogger Emily Gould—essentially a real-­life Hannah Horvath—realized this during her two-­year struggle to get a novel published. Though she had a six-­figure book deal, she was stuck. Why? She was too busy “spending a lot of time on the Internet,” that’s why.

“In fact, I can’t really remember anything else I did in 2010. I tumbld, I tweeted and I scrolled. This didn’t earn me any money but it felt like work… It was also the only creative thing I was doing.”

She did what a lot of us do when we’re scared or overwhelmed by a project—she did everything but focus on it. In fact, many valuable endeavors we undertake are painfully difficult, whether it’s coding a new startup or mastering a craft. But talking, talking is always easy. So we do that instead.

It’s a temptation that exists for everyone—for talk and hype to replace action.

Doing great work is a struggle. It’s draining, it’s demoralizing, it’s frightening—not always, but it can feel that way when we’re deep in the middle of it. We talk to fill the void and the uncertainty.

The question is, when faced with your particular challenge—­whether it is researching in a new field, starting a business, producing a film, securing a mentor, advancing an important cause—do you seek the respite of talk or do you face the struggle head­-on?

2. Early pride.

At 18, a rather triumphant Benjamin Franklin returned to visit Boston, the city he’d run away from. Full of pride, he had a new suit, a watch and a pocketful of coins that he showed to everyone he ran into. All posturing by a boy who was not much more than an employee in a print shop in Philadelphia.

In a meeting with Cotton Mather, one of the town’s most respected figures, Franklin quickly illustrated just how ridiculously inflated his young ego had become. As they walked down a hallway, Mather suddenly admonished him, “Stoop! Stoop!” Too caught up in his performance, Franklin walked right into a low ceiling beam.

Mather’s response was perfect: “Let this be a caution to you not always to hold your head so high,” he said wryly. “Stoop, young man, stoop—as you go through this world—and you’ll miss many hard thumps.”

The problem with pride is that it blunts the instrument we need to succeed—our mind. Our ability to learn, to adapt, to be flexible, to build relationships, all of this is dulled by pride. Most dangerously, this tends to happen either early in life or in the process—­when we’re flushed with beginner’s conceit. Only later do you realize that that bump on the head was the least of what was risked.

The question to ask, when you feel pride, then, is this: What am I missing right now that a more humble person might see? What am I avoiding, or running from, with my bluster, franticness, and embellishments?

It is far better to ask and answer these questions now, with the stakes still low, than it will be later.

3. Don’t be passionate.

Early on in her ascendant political career, a visitor once spoke of Eleanor Roosevelt’s “passionate interest” in a piece of social legislation. The person had meant it as a compliment. But Eleanor’s response is illustrative. “Yes,” she did support the cause, she said. “But I hardly think the word ‘passionate’ applies to me.” As a genteel, accomplished, and patient woman born while the embers of the quiet Victorian virtues were still warm, Roosevelt was above passion. She had purpose and direction.

Today it’s all about passion. Find your passion. Live passionately. Inspire the world with your passion.

People go to Burning Man to find passion, to be around passion, to rekindle their passion. Same goes for TED and the now enormous SXSW and a thousand other events, retreats and summits, all fueled by what they claim to be life’s most important force.

Here’s what those same people haven’t told you: your passion may be the very thing holding you back from power or influence or accomplishment. Because just as often, we fail with—no, because of—passion. To be clear, this is not about caring. This is passion of a different sort—unbridled enthusiasm, our willingness to pounce on what’s in front of us with the full measure of our zeal, the “bundle of energy” that our teachers and gurus have assured us is our most important asset.

Instead, what we require in our ascent is purpose. Purpose, you could say, is like passion with boundar­ies. Passion is form over function. Purpose is function, function, function. The critical work that you want to do will require your deliberation and consideration. Not passion.

Passion is about. (I am so passionate about ______.) Purpose is to and for. (I must do ______. I was put here to accomplish ______. I am willing to endure ______ for the sake of this.) Actually, purpose deemphasizes the I.

Purpose is about pursuing something outside yourself as opposed to pleasuring yourself. “Great passions are maladies without hope,” as Goethe said. Which is why a deliberate, purposeful person operates on a different level, beyond the sway or the sickness.

It’d be far better if you were intimidated by what lies ahead—humbled by its magnitude and determined to see it through regardless. Leave passion for the amateurs. Make it about your purpose: what you feel you must do and say, not what you care about and wish to be. Then you will do great things. Then you will stop being your old, good-­intentioned, but ineffective self.

Early on in our careers we are setting out to do something. We have a goal, a calling, a new beginning. Every great journey begins here—yet far too many of us never reach our intended destination. Ego more often than not is the culprit.

We build ourselves up with fantastical stories and talk, we pretend we have it all figured out, we let our star burn bright and hot only to fizzle out, and we have no idea why. These are symptoms of ego, for which humility and reality are the cure.

Do not let ego derail your career—before it even begins.

This piece is adapted from Ryan Holiday’s book Ego is the Enemy, published by Penguin Portfolio.

Sometimes there is nothing like a 900-page biography. Most of the time though, nobody has time for such a thing. Especially with many modern biographers who refuse to take a stand that resembles judgement towards their subjects.

After all, we read biographies to learn and improve ourselves, not to simply accumulate facts about someone we’ll never meet.

This leads to one of my favorite categories of books I like to recommend: moral biographies. That is, short biographical sketches about great men and women in history, written with an eye towards practical application and advice. As in, have a moral rather than about morality. They are often more anecdotal than historical, apocryphal than accurate but they get the job done. (Incidentally, this was the model I tried to base my book The Obstacle Is The Way on, though I hardly consider myself in the same league.)

Below are some of my favorites. I hope you enjoy them.

How They Succeeded: Life Stories of Successful Men Told By Themselves by Orison Swett Marden Written in 1901 these are uplifting business oriented biographies of men like Marshall Field, John D Rockefeller, Alexander Graham Bell and Thomas Edison and women like Helen Gould and Julia Ward Howe (creator of Battle Hymn of the Republic). I was referred this book by Maria Popova over at Brainpickings and loved it—I’ve referred to it many times since reading it.

Lives of Eminent Philosophers Volumes I & II by Diogenes Laertius Ironically, Diogenes’ most famous biography in this collection is of the other Diogenes—Diogenes the Cynic. Other excellent and illustrative sketches include Zeno, Ariston, Cleanthes and Chrysippus the Stoic. Heraclitus is another great biography. All of these vary in length. Zeno is over 150 pages, Herillus (not to be confused with Heraclitus) is 2 pages. But regardless of length, they are all quite good. My favorite little quirk of the book is Diogenes’ weird poem that he writes about each philosopher and of course the credulity with which he reports on their unusual deaths (on that note, you may also like the book The Book of Dead Philosophers, a book on how many of the world’s most famous philosophers supposedly died.)

Lives of the Later Caesars by Anonymous Written by an anonymous author (possibly multiple) in the 4th century, these biographies are a mix of myth, legend and fact about some of the most powerful men who ever lived: the Roman emperors. We have Hadrian, Marcus Aurelius, Trajan, Avidius Cassius, Severus and countless others. I’m sure you can guess my favorite subject. Also try The Twelve Caesars by Suetonius, translated by the peerless Robert Graves, these are more biographies of the Roman emperors—from Julius Ceasar to Domitian.

Plutarch’s LivesClearly the master of this genre, Plutarch wrote biographies of famous Greeks and Romans around the year 100 AD. As always, I tend to default to the Penguin collections. I strongly recommend Plutarch’s Lives Vol. I & II, Essays, and The Makers of Rome: Nine Lives. His book On Sparta is also a collection of biographies (and aphorisms) from the famous Spartans. There is a reason that Shakespeare based many of his plays on Plutarch—not only are they well-written and exciting but they exhibit everything that is good and bad about the human condition. Greed, love, pain, hate, success, selflessness, leadership, stupidity—it’s all there.

The Works of Robert GreeneYou can argue that the master heir to this tradition is Robert Greene. What is the 48 Laws of Power but a series of biographies—moral lessons—from interesting figures in history? Naturally when I say moral I don’t mean morality, I mean the stories have a moral. From Robert Greene you can learn about Napoleon, Machiavelli, Cortez, Julius Caesar, Alexander the Great, FDR, Temple Grandin, PT Barnum, and 50 Cent in an accessible way that is really quite difficult to replicate anywhere else.

Profiles in Courage by John F. Kennedy Written by President Kennedy when he was bedridden after back surgery, Profiles in Courage recounts the inspiring acts of eight different American Senators, including John Quincy Adams, Daniel Webster, Sam Houston, and Robert A. Taft. Kennedy had recently been elected as the junior Senator from Massachusetts and was inspired to write a book after reading a passage from The Price of Union about an act of courage by John Quincy Adams while serving in the Senate. It was heartening to read about Senators willing to cross party lines and stand up for their principles given the current state of our Congress.

The Lives of the Most Excellent Painters, Sculptors, and Architects by Giorgio Vasari A friend and peer of Michelangelo, Da Vinci, Raphael Titian and all the other great minds of the Renaissance sat down in 1550 and wrote biographical sketches of the people he knew or had influenced him. What I like about this book is that the profiles are not about statesmen or generals but artists. There are so many great lessons about craft and psychology within this book. The best part? It was written by someone who actually knew what he was talking about, not some art snob or critic, but an actual artist and architect of equal stature to the people he was documenting.

Founders At Work: Stories of Startups’ Early Daysby Jessica Livingston Now this one is certainly a little less historical than the others, if only because most of the profiles are about companies founded in the last ten years. Written by Jessica Livingston, a founder of YCombinator, the book profiles some of the hottest and most successful startups in Silicon Valley history. It shows how the founders managed to create massive growth, usually with very few resources. Now I’m not saying that companies like Hot or Not compare with the accomplishments of Pericles or Da Vinci, but you can certainly see how this book captures a moment in time—and its leading men and women—and what that means. This is the most current book on the list (besides mine) but I think many of you will like it. Plus you can learn a lot about the tech scene in one swoop.

If you never took a history course, hell if your parents never taught you anything, these little books could help. They show us how to live and how not to live. And best of all, you can read about a bunch of different people in one book.

What we choose to do with that information is up to us, of course. I hope you all use it wisely and get as much out of it as I did.

And if you have room for another book of such stories, try my book The Obstacle Is The Way for stories about Amelia Earhart, Arthur Ashe, Thomas Edison, John D. Rockefeller, Dwight D. Eisenhower, and Abraham Lincoln.